Triethylamine → tert-Butyl {methyl[6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyrimidinyl]amino}acetate

HRID 748380Notes

Reaction equation

HRID 748380 reaction equation
[CH3:1][N:2]([CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:3]1[N:8]=[CH:7][CH:6]=[C:5]([C:9]#[N:10])[N:4]=1.[C:19](OC)(=[O:27])[C:20]1[C:21](=[CH:23][CH:24]=[CH:25][CH:26]=1)[SH:22].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:1][N:2]([CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:3]1[N:8]=[CH:7][CH:6]=[C:5]([C:9]2[S:22][C:21]3[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=3[C:19](=[O:27])[N:10]=2)[N:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 70859672tert-Butyl [methyl(6-cyano-2-pyrimidinyl)amino]acetate

Product 1

HCID 59750482tert-Butyl {methyl[6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyrimidinyl]amino}acetateYield 47.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

tert-Butyl [methyl(6-cyano-2-pyrimidinyl)amino]acetate (1.63 g, 6.56 mmol) and methyl thiosalicylate (3.31 g, 19.7 mmol) were dissolved in toluene (50 ml), and triethylamine (2.76 ml, 19.7 mmol) was added thereto. The mixture was refluxed for 18 hrs. The solvent was evaporated, and the residue was recrystallized from ethanol to give the titled compound (1.20 g, 39%) as pale yellow crystals.

Workup

  1. temperatureThe mixture was refluxed for 18 hrs
  2. customThe solvent was evaporated
  3. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-2a8c2094780347a0b38f5d1d00ce8ddf
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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